Men of Style

Chosen One

Milo Ventimiliglia on the art of the pocket square, the power of lasting style, and his hit series on Crackle.

Some actors have style thrust upon them via much needed help from a stylist. Others come by it naturally, over time, exploring and experimenting their way to a look and level of taste that’s both lasting and deeply personal. Milo Ventimiglia, star of Chosen on Crackle, is firmly in the latter category. Check out his take jewelry, learning to hold a handgun, and developing your own sense of personal style, and shop the looks he’s wearing Saturday, February 22 at noon ET.

Virtually the first thing you did when you walked in here was school us on the art of the pocket square. Where did you learn those skills?
[Laughs.] When I was two or three I walked out of my parents’ room wearing a loosely tied tie. My mom was like, ‘Did your dad do that for you!?’ Apparently he was outside and had no idea. So watching my dad dress growing up, he always looked sharp in a suit, so I always had this sense of how I’d put myself together. And as you get older you pick up little bits and pieces — a tie bar, a pocket square, a ring, a watch, a chain, no matter what it is, you pick up these little things and it’s validated when two or three or four years later you see these big companies starting to cycle through those things.

You’ve been out there in the public eye for a while now. Are there any style mistakes in your past you’d love to forget?
A beaded necklace when I was 18, but it was something that I made — and it wasn’t like somebody else was telling me to wear it. I’ve always had a strong will to say, ‘You know, thank you very much, but I don’t think I like this.’ So if anything they were all my own mistakes. Or lessons learned. Let’s call them lessons learned.

So there was no denim tux and cowboy hat, a la Justin Timberlake, lurking out there.
[laughs] No, no. At an early age I hit that point where I thought, you shouldn’t be able to tell when the photo was taken by what I’m wearing. When you look at the images of old Hollywood, there’s something timeless about them, so it’s like the clothes reflect that ageless era. So that was something I’ve always tried to do.

Let’s talk Chosen — I hear it’s coming back for a third season.
We just wrapped the third season, with Rose McGowan. It was more explosive, more intense, more heartfelt, more heartbreaking going into the second and the third seasons.

It’s based on an electrifying premise. For guys who don’t know the show, what’s the elevator pitch?
You get a box on your doorstep and in it is a photograph of a person you’ve never met before, with an expiration date, and a gun. And you’re expected to kill that person. What you find out very quickly is that somebody’s out there with a box with your face in it as well. So it’s a hunt and be hunted game. Every day normal people get chosen — a school teacher can be chosen or an attorney like my character can be chosen or a sick maniacal evil twisted person can be chosen and they could embrace the art of killing and being a killer.

Did you have to learn to hold a handgun with some credibility? I feel like that’s one of those skills every young actor ought to master.
The funny thing was that my character in the first season was an attorney and had never held a weapon, so the first moment when I’m actually having to lock the magazine into the gun I do it backwards and it’s not working and I’m fussing with it, but then as an actor you kind of have to be like, “Alright, how do I build the character to where he is comfortable or he is aware of how to use a gun.” My character goes on YouTube to learn how to lock and load a weapon.

There’s a lot of talk about how streaming is really changing how people watch TV, binge watching and all that.
We’ll shoot six episodes, which is our entire season, and we’ll just let them go right off the bat. From what I’ve heard from people, everybody’s saying the second that first one goes — boom, they’re hooked, and they’re along for the ride all the way to the end. I think it’s a benefit not having to wait around like with normal television.

You are clearly a guy who’s always on the hunt for cool things. I bet you’ve got a badass car.
I’ve got a classic car, a ‘67 Chevelle Super Sport. I’ve also got a Harley Davidson. But you know, I’ve gotten to the point in my life where I know the things I like, and I don’t have to be excessive about it. I’ve got my nice collection pieces. Anyting from a vintage peacoat to an old car. It even boils down to the restaurants you go to.

Absolutely. It gets to that point where you apply a connoisseur’s approach to it. It’s about fewer things but better things. I love your rings. Tell me about them.
The turquoise one is a 1950s Zuny wedding band that I picked up from my friends over at RRL in Los Angeles. And then the other one, my Indian chief, is by a friend of mine, Jessica Seaton. I’d always been a fan of her stuff, but I was never a ring kind of guy — maybe a chain with medallions from my grandmother, or a simple watch that was my dad’s in Vietnam. But then I saw this Indian chief ring, and it’s funny she told you, ‘You’re one of the guys I thought would wear it.” I got the first one off the press and now I wear it all the time.

We’ve profiled a ton of cool guys, from Billy Reid to Amar’e Stoudemire. Who should we hit up as our next Man of Style?
There’s a director whose name is Anthony Mandler, he does a lot in the music world and he’s a photographer, but he’s a guy who has a very casual, effortless way about him, but it’s also put together, but you can tell he’s not trying, it’s just who he is. He’s a cool guy.

I think it starts with being a cool guy first, doesn’t it?
First and foremost, because you don’t want anybody complimenting the asshole just because he’s well-dressed. [laughs]

Shop spring suiting modeled by Milo Ventimiglia on Gilt >>

Watch Milo in ‘Chosen’ on Crackle >>

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